cis-2-hydroxymethyl-5-phenyl-1-p-toluenesulfonylpyrrolidine

Base Information

• Chemical Name: cis-2-hydroxymethyl-5-phenyl-1-p-toluenesulfonylpyrrolidine
• CAS No.: 137401-55-9
• Molecular Formula: C₁₈H₂₁NO₃S
• Molecular Weight: 331.436
• Mol file: 137401-55-9.mol

Synonyms:cis-2-hydroxymethyl-5-phenyl-1-p-toluenesulfonylpyrrolidine

Chemical Property of cis-2-hydroxymethyl-5-phenyl-1-p-toluenesulfonylpyrrolidine

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

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Technology Process of cis-2-hydroxymethyl-5-phenyl-1-p-toluenesulfonylpyrrolidine

There total 10 articles about cis-2-hydroxymethyl-5-phenyl-1-p-toluenesulfonylpyrrolidine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

C27H38N2O3S → cis-2-hydroxymethyl-5-phenyl-1-p-toluenesulfonylpyrrolidine (137401-55-9)

Guidance literature:

With ammonium chloride; zinc; In methanol; water; at 90 ℃; for 24h; Sealed tube;

DOI:10.1021/acs.orglett.1c01148

Reference yield:

2-(benzyldimethylsilyl)methyl-5-phenyl-1-p-toluenesulfonylpyrrolidine → trans-2-hydroxymethyl-5-phenyl-1-p-toluenesulfonylpyrrolidine + cis-2-hydroxymethyl-5-phenyl-1-p-toluenesulfonylpyrrolidine (137401-55-9)

Guidance literature:

With tetrabutyl ammonium fluoride; dihydrogen peroxide; potassium hydrogencarbonate; In tetrahydrofuran; methanol; water; at 40 ℃; Title compound not separated from byproducts.;

DOI:10.1021/ol991341o

Reference yield:

N-benzylidene benzylamine (780-25-6) → cis-2-hydroxymethyl-5-phenyl-1-p-toluenesulfonylpyrrolidine (137401-55-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 1) LDA / 1) THF, -78 deg C, 2 h, 2) to RT

2: 42 percent / pyridine / -10 °C

3: 92 percent / AgBF₄ / CH₂Cl₂ / Ambient temperature; further allenic sulphonamides

4: 1) ozone, 2) NaBH₄ / 1) MeOH, -78 deg C, 2) to RT

With pyridine; sodium tetrahydroborate; silver tetrafluoroborate; ozone; lithium diisopropyl amide; In dichloromethane;

upstream raw materials:

rac-(2R,5S)-1-[(4-methylphenyl)sulfonyl]-2-phenyl-5-vinylpyrrolidine

N-benzylidene benzylamine

N-1-phenyl-N-tosylhexa-4,5-dienylamine

p-toluenesulfonyl chloride

Downstream raw materials:

cis-5-phenyl-N-tosylpyrrolidin-2-ylmethyl 4 bromobenzoate

Refernces

• 1、 Miura, Katsukiyo,Hondo, Takeshi,Nakagawa, Takahiro,Takahashi, Tatsuyuki,Hosomi, Akira. "Acid-catalyzed cyclization of vinylsilanes bearing an amino group. Stereoselective synthesis of pyrrolidines". . p. 385 - 388. Retrieved 2007/10/03.